Abrasive-filled thermoset composition and its preparation, and abrasive-filled articles and their preparation

ABSTRACT

A curable resin composition comprises a poly(arylene ether), an acryloyl monomer, an allylic monomer, and an abrasive filler. The composition tolerates high filler contents, cures rapidly, and exhibits excellent toughness after curing. Useful articles prepared from the composition include grinding wheels and cut-off wheels having good wear characteristics.

BACKGROUND OF INVENTION

Abrasive-filled resins are known and employed in the fabrication ofabrasive tools such as cutting and grinding wheels. Grinding wheelscontaining superabrasive materials (e.g., diamond or cubic boronnitride, CBN) in the edge or outer periphery of a circular grindingwheel or grinding cup also are well-known in the fields of sawing,drilling, dressing, grinding, lapping, polishing, and other abradingapplications. For these applications, the grit typically is surroundedin a matrix of a metal, such as Ni, Cu, Fe, Co, Sn, W, Ti, or an alloythereof, or in a resin, such as phenol formaldehyde or otherthermosetting polymeric material. By attaching the matrices to a body orother support, tools may be fabricated having the capability to cutthrough such hard, abrasive materials as concrete, asphalt, masonry,ceramic, brick, granite, marble, and other rock. A typical such wheel isformed from a central metal disk having an aperture or a spindle forspinning the wheel in use. The outer periphery of the wheel, then, has adiamond-containing matrix bonded thereto. For wheels where the diamondis surrounded by a resin, the operator often cures the resin and bondsthe resinous segments to the inner wheel by compression molding.Conventional bonding resins are used.

U.S. Pat. No. 5,167,674 describes grinding wheels manufactured from aconventional inner core to which is adhesively bonded a mixture ofsuperabrasive grit, a bis-maleimide-triazine addition copolymer resin,free-radical initiator, and catalyst. This mixture is compression moldedto form a grinding segment annulus.

U.S. Pat. No. 5,314,512 describes injection molding of saw segments fromsuperabrasive particles and a non-porous thermoplastic polymer. Themolded saw segments then are affixed to the periphery of a saw blade.

European Patent No. 794,850 B1 describes cutting segments manufacturedfrom superabrasive particles molded with a thermoplastic materialwherein the superabrasive particles are oriented in a chosen directionand there is porosity in the molded segments.

U.S. Pat. Nos. 4,054,425 and 4,088,729 describe molding a hub into aphenol-based thermoplastic resin-grinding wheel.

U.S. Pat. No. 3,960,516 describes manufacturing a grinding cup whereinthe supporting part is molded as a part of the grinding cup to ensure asecure attachment.

There is a need for curable, abrasive-filled resin compositions thatallow fast preparation of cutting and grinding tools having improvedwear characteristics.

SUMMARY OF INVENTION

Disclosed herein are several embodiments of a resin composition, itsreaction product, a method for its preparation, and articles derivedfrom it.

In one embodiment, a curable resin composition comprises a poly(aryleneether), an acryloyl monomer, an allylic monomer, and an abrasive filler.

In another embodiment, a cured resin composition comprises the reactionproduct of a poly(arylene ether), an acryloyl monomer, an allylicmonomer, and an abrasive filler.

Yet another embodiment is a method of preparing the curable resincomposition.

Still other embodiments are articles comprising the cured resincomposition and methods for their preparation.

DETAILED DESCRIPTION

A curable resin composition comprises a poly(arylene ether), an acryloylmonomer, an allylic monomer, and an abrasive filler.

The composition may comprise any poly(arylene ether). The termpoly(arylene ether) includes polyphenylene ether (PPE) and poly(aryleneether) copolymers; graft copolymers; poly(arylene ether) ether ionomers;and block copolymers of alkenyl aromatic compounds, vinyl aromaticcompounds, and poly(arylene ether), and the like; and combinationscomprising at least one of the foregoing; and the like. Poly (aryleneether)s are known polymers comprising a plurality of structural units ofthe formula:

wherein for each structural unit, each Q¹ is independently halogen,primary or secondary C₁-C₁₂ alkyl, phenyl, C₁-C₁₂ haloalkyl, C₁-C₁₂aminoalkyl, C₁-C₁₂ hydrocarbonoxy, or C₂-C₁₂ halohydrocarbonoxy whereinat least two carbon atoms separate the halogen and oxygen atoms; andeach Q² is independently hydrogen, halogen, primary or secondary C₁-C₁₂alkyl, phenyl, C₁-C₁₂ haloalkyl, C₁-C₁₂ aminoalkyl, C₁-C₁₂hydrocarbonoxy, or C₂-C₁₂ halohydrocarbonoxy wherein at least two carbonatoms separate the halogen and oxygen atoms. Preferably, each Q¹ isindependently C₁-C₁₂ alkyl or phenyl, especially C₁₋₄ alkyl, and each Q²is independently hydrogen or methyl.

Both homopolymer and copolymer poly(arylene ether)s are included. In oneembodiment, the poly(arylene ether) is a homopolymer comprising2,6-dimethyl-1,4-phenylene ether units. Suitable copolymers includerandom copolymers comprising, for example, such units in combinationwith 2,3,6-trimethyl-1,4-phenylene ether units or copolymers derivedfrom copolymerization of 2,6-dimethylphenol with 2,3,6-trimethylphenol.Also included are poly(arylene ether)s containing moieties prepared bygrafting vinyl monomers or polymers such as polystyrenes, as well ascoupled poly(arylene ether) in which coupling agents such as lowmolecular weight polycarbonates, quinones, heterocycles and formalsundergo reaction with the hydroxy groups of two poly(arylene ether)chains to produce a higher molecular weight polymer. Poly(aryleneether)s further include combinations of any of the above.

The poly(arylene ether)s are typically prepared by the oxidativecoupling of at least one monohydroxyaromatic compound such as2,6-xylenol or 2,3,6-trimethylphenol. Catalyst systems are generallyemployed for such coupling; they typically contain at least one heavymetal compound such as a copper, manganese or cobalt compound, usuallyin combination with various other materials. Suitable methods for thepreparation and isolation of poly(arylene ether)s are disclosed in, forexample, U.S. Pat. Nos. 3,219,625 to Blanchard et al., 3,306,875 to Hay,4,028,341 to Hay, 4,092,294 to Bennett, Jr. et al., 4,440,923 toBartmann et al., and 5,922,815 to Aycock et al.

In one embodiment, the composition comprises a poly(arylene ether)having less than 500 parts per million (ppm) of free hydroxyl groups. Inother words, the poly(arylene ether) contains less than 500 microgramsof hydroxyl groups (as —OH) per gram of poly(arylene ether). Thepoly(arylene ether) preferably comprises less than 300 ppm of freehydroxyl groups, more preferably less than 100 ppm of free hydroxylgroups.

In one embodiment, the composition comprises a capped poly(aryleneether), which is defined herein as a poly(arylene ether) in which atleast 50%, preferably at least 75%, more preferably at least 90%, yetmore preferably at least 95%, even more preferably at least 99%,of thefree hydroxyl groups present in the corresponding uncapped poly(aryleneether) have been removed by reaction with a capping agent.

The capped poly(arylene ether) may be represented by the structureQ-(J-K)y wherein Q is the residuum of a monohydric, dihydric, orpolyhydric phenol, preferably the residuum of a monohydric or dihydricphenol, more preferably the residuum of a monohydric phenol; y is 1 to100; J comprises recurring units having the structure

wherein m is 1 to about 200, preferably 2 to about 200, and R¹-R⁴ areeach independently hydrogen, halogen, primary or secondary C₁-C₁₂ alkyl,C₂-C₁₂ alkenyl, C₂-C₁₂ alkynyl, C₁-C₁₂ aminoalkyl, C₁-C₁₂ hydroxyalkyl,phenyl, C₁-C₁₂ haloalkyl, C₁-C₁₂ aminoalkyl, C₁-C₁₂ hydrocarbonoxy,C₂-C₁₂ halohydrocarbonoxy wherein at least two carbon atoms separate thehalogen and oxygen atoms, or the like; and K is a capping group producedby reaction of the phenolic hydroxyl groups on the poly(arylene ether)with a capping reagent. The resulting capping group may be

wherein R⁵ is C₁-C₁₂ alkyl; R⁶-R⁸ are each independently hydrogen,C₁-C₁₂ alkyl, C₂-C₁₂ alkenyl, C₆-C₁₈ aryl, C₇-C₁₈ mixed (alkyl-aryl),C₂-C₁₂ alkoxycarbonyl, C₇-C₁₈ aryloxycarbonyl, C₈-C₁₈ mixed (alkyl-aryl)oxycarbonyl, nitrile, formyl, carboxylate, imidate, thiocarboxylate, orthe like; R⁹-R¹³ are each independently hydrogen, halogen, C₁-C₁₂ alkyl,hydroxy, amino, or the like; and wherein Y is a divalent group havingthe structure

wherein R¹⁴ and R¹⁵ are each independently hydrogen, C₁-C₁₂ alkyl, orthe like.

In one embodiment, Q is the residuum of a phenol, includingpolyfunctional phenols, and includes radicals of the structure

wherein R¹-R⁴ are each independently hydrogen, halogen, primary orsecondary C₁-C₁₂ alkyl, C₂-C₁₂ alkenyl, C₂-C₁₂ alkynyl, C₁-C₁₂aminoalkyl, C₁-C₁₂ hydroxyalkyl, phenyl, C₁-C₁₂ haloalkyl, C₁-C₁₂aminoalkyl, C₁-C₁₂ hydrocarbonoxy, C₂-C₁₂ halohydrocarbonoxy wherein atleast two carbon atoms separate the halogen and oxygen atoms, or thelike; X is hydrogen, C₁-C₂₀ alkyl, C₆-C₂₀ aryl, C₇-C₂₀ mixed alkyl-arylhydrocarbons, or such hydrocarbon groups containing a substituent suchas carboxylic acid, aldehyde, alcohol, amino, or the like; X also may besulfur, sulfonyl, sulfuryl, oxygen, or other such bridging group havinga valence of 2 or greater to result in various bis-or higherpolyphenols; y and n are each independently 1 to about 100, preferably 1to 3, and more preferably 1 to 2. In a preferred embodiment, y=n.

In one embodiment, the capped poly(arylene ether) is produced by cappinga poly(arylene ether) consisting essentially of the polymerizationproduct of at least one monohydric phenol having the structure

wherein R¹-R⁴ are each independently hydrogen, halogen, primary orsecondary C₁-C₁₂ alkyl, C₂-C₁₂ alkenyl, C₂-C₁₂ alkynyl, C₁-C₁₂aminoalkyl, C₁-C₁₂ hydroxyalkyl, phenyl, C₁-C₁₂ haloalkyl, C₁-C₁₂aminoalkyl, C₁-C₁₂ hydrocarbonoxy, C₂-C₁₂ halohydrocarbonoxy wherein atleast two carbon atoms separate the halogen and oxygen atoms, or thelike. Suitable monohydric phenols include those described in U.S. Pat.No. 3,306,875 to Hay, and highly preferred monohydric phenols include2,6-dimethylphenol and 2,3,6-trimethylphenol.

In one embodiment, the capped poly(arylene ether) comprises at least onecapping group having the structure

wherein R⁶-R⁸ are each independently hydrogen, C₁-C₁₂ alkyl, C₂-C₁₂alkenyl, C₆-C₁₈ aryl, C₇-C₁₈ mixed (alkyl-aryl), C₂-C₁₂ alkoxycarbonyl,C₇-C₁₈ aryloxycarbonyl, C₈-C₁₈ mixed (alkyl-aryl)oxycarbonyl, nitrile,formyl, carboxylate, imidate, thiocarboxylate, or the like. Highlypreferred capping groups include acrylate (R⁶═R⁷═R⁸═hydrogen) andmethacrylate (R⁶═methyl, R⁷═R⁸═hydrogen).

In one embodiment, the capped poly(arylene ether) comprises at least onecapping group having the structure

wherein R⁵ is C₁-C₁₂ alkyl, preferably C₁-C₆ alkyl, more preferablymethyl, ethyl, or isopropyl. It has surprisingly been found that theadvantageous properties of the composition can be achieved even when thecapped poly(arylene ether) lacks a polymerizable function such as acarbon-carbon double bond.

In another embodiment, the capped poly(arylene ether) comprises at leastone capping group having the structure

wherein R⁹-R¹³ are each independently hydrogen, halogen, C₁-C₁₂ alkyl,hydroxy, amino, or the like. Preferred capping groups of this typeinclude salicylate (R⁹ is hydroxy, and R¹⁰-R¹³ are hydrogen).

In one embodiment, the capped poly(arylene ether) is substantially freeof amino substituents, including alkylamino and dialkylaminosubstituents, wherein substantially free means that the cappedpoly(arylene ether) contains less than about 300 micrograms, preferablyless than about 200 micrograms, more preferably less than about 100micrograms, of atomic nitrogen per gram of capped poly(arylene ether).Although many poly(arylene ether)s are synthesized by processes thatresult in the incorporation of amino substituents, it has beendiscovered that thermoset curing rates are increased when the cappedpoly(arylene ether) is substantially free of amino substituents.Poly(arylene ether)s substantially free of amino substituents may besynthesized directly or generated by heating amino-substitutedpoly(arylene ether)s to at least about 200° C. Alternatively, if thecapped poly(arylene ether) contains amino substituents, it may bedesirable to cure the composition at a temperature less than about 200°C.

There is no particular limitation on the method by which the capped poly(arylene ether) is prepared. The capped poly(arylene ether) may beformed by the reaction of an uncapped poly(arylene ether) with a cappingagent. Capping agents include compounds that react with phenolic groups.Such compounds include both monomers and polymers containing, forexample, anhydride groups, acid chloride groups, epoxy groups, carbonategroups, ester groups, isocyanate groups, cyanate ester groups, alkylhalide groups, or combinations comprising at least one of the foregoinggroups. Capping agents are not limited to organic compounds as, forexample, phosphorus and sulfur based capping agents also are included.Examples of capping agents include, for example, acetic anhydride,succinic anhydride, maleic anhydride, salicylic anhydride, polyesterscomprising salicylate units, homopolyesters of salicylic acid, acrylicanhydride, methacrylic an hydride, glycidyl acrylate, glycidylmethacrylate, acetyl chloride, benzoyl chloride, diphenyl carbonatessuch as di(4-nitrophenyl)carbonate, acryloyl esters, methacryloylesters, acetyl esters, phenylisocyanate,3-isopropenyl-alpha,alpha-dimethylphenylisocyanate, cyanatobenzene,2,2-bis(4-cyanatophenyl)propane), 3-(alpha-chloromethyl)styrene,4-(alpha-chloromethyl)styrene, allyl bromide, and the like, carbonateand substituted derivatives thereof, and mixtures comprising at leastone of the foregoing capping agents. These and other methods of formingcapped poly(arylene ether)s are described, for example, in U.S. Pat.Nos. 3,375,228 to Holoch et al.; 4,148,843 to Goossens; 4,562,243,4,663,402, 4,665,137, and 5,091,480 to Percec et al.; 5,071,922,5,079,268, 5,304,600, and 5,310,820 to Nelissen et al.; 5,338,796 toVianello et al.; and European Patent No. 261,574 B1 to Peters et al.

A capping catalyst may be employed in the reaction of an uncapped poly(arylene ether) with an anhydride. Examples of such compounds includethose that are capable of catalyzing condensation of phenols with thecapping agents described above. Useful materials are basic compoundsincluding, for example, basic compound hydroxide salts such as sodiumhydroxide, potassium hydroxide, tetraalkylammonium hydroxides, and thelike; tertiary alkyl amines such as tributyl amine, triethylamine,dimethylbenzylamine, dimethylbutylamine, and the like; tertiary mixedalkyl-arylamines and substituted derivatives thereof such asdimethylaniline, and the like; heterocyclic amines such as imidazoles,pyridines, and substituted derivatives thereof such as2-methylimidazole, 2-vinylimidazole, 4-(dimethylamino)pyridine,4-(1-pyrrolino)pyridine, 4-(1-piperidino)pyridine, 2-vinylpyridine,3-vinylpyridine, 4-vinylpyridine, and the like; and mixtures comprisingat least one of the foregoing materials. Also useful are organometallicsalts such as, for example, tin and zinc salts known to catalyze thecondensation of, for example, isocyanates or cyanate esters withphenols. The organometallic salts useful in this regard are known to theart in numerous publications and patents well known to those skilled inthis art.

The composition may comprise a blend of at least two capped poly(aryleneethers). Such blends may be prepared from individually prepared andisolated capped poly(arylene ethers). Alternatively, such blends mayprepared by reacting a single poly(arylene ether) with at least twocapping agents.

There is no particular limitation on the molecular weight or intrinsicviscosity of the poly(arylene ether). In one embodiment, the intrinsicviscosity, as measured in chloroform at 25° C., may be at least about0.1 deciliters/gram (dL/g), preferably at least about 0.1 5 dL/g, morepreferably at least about 0.20 dL/g. The intrinsic viscosity may be upto about 0.50 dL/g, preferably up to about 0.45 dL/g, more preferably upto about 0.40 dL/g, yet more preferably up to about 0.35 dL/g.Generally, the intrinsic viscosity of a capped poly(arylene ether) willvary insignificantly from the intrinsic viscosity of the correspondinguncapped poly (arylene ether). It is expressly contemplated to employblends of at least two capped poly(arylene ether)s having differentmolecular weights and intrinsic viscosities.

The composition may comprise the poly(arylene ether) in an amount of atleast about 10 parts by weight, preferably at least about 15 parts byweight, more preferably at least about 20 parts by weight per 100 partsby weight resin. The composition may comprise the poly(arylene ether) inan amount up to about 50 parts by weight, preferably up to about 45parts by weight, more preferably up to about 40 parts by weight per 100parts by weight resin. It will be understood that “100 parts by weightresin” as used herein refers to the combined parts by weight of resinouscomponents such as the poly(arylene ether), the acryloyl monomer, andthe allylic monomer; it excludes non-resinous components such as theabrasive filler, and any secondary filler or curing catalyst.

The composition further comprises an acryloyl monomer. The acryloylmonomer comprises at least one acryloyl moiety having the structure

wherein R¹⁶ and R¹⁷ are each independently hydrogen or C₁-C₁₂ alkyl, andwherein R¹⁶ and R¹⁷ may be disposed either cis or trans about thecarbon-carbon double bond. Preferably, R¹⁶ and R¹⁷ are eachindependently hydrogen or methyl. In one embodiment, the acryloylmonomer comprises at least two acryloyl moieties having the abovestructure. In another embodiment, the acryloyl monomer comprises atleast three acryloyl moieties having the above structure.

In one embodiment, the acryloyl monomer comprises at least one acryloylmoiety having the structure

wherein R¹⁸-R²⁰ are each independently hydrogen, C₁-C₁₂ alkyl, C₂-C₁₂alkenyl, C₆-C₁₈ aryl, C₇-C₁₈ mixed (alkyl-aryl), C₂-C₁₂ alkoxycarbonyl,C₇-C₁₈ aryloxycarbonyl, C₈-C₁₈ mixed (alkyl-aryl)oxycarbonyl, nitrile,formyl, carboxylate, imidate, thiocarboxylate, or the like. Preferably,R¹⁸-R²⁰ are each independently hydrogen or methyl. In one embodiment,the acryloyl monomer comprises at least two acryloyl moieties having thestructure above. In another embodiment, the acryloyl monomer comprisesat least three acryloyl moieties having the structure above.

Suitable acryloyl monomers include, for example, methyl (meth)acrylate,ethyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate,isobutyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, 2-hydroxyethyl(meth)acrylate, 3-hydroxypropyl (meth)acrylate, hydroxybutyl(meth)acrylate, glycidyl (meth)acrylate, 2,2-dimethyl-3-hydroxypropyl(meth)acrylate, isobornyl (meth)acrylate, tetrahydrofurfuryl(meth)acrylate, 3,4-epoxycyclohexylmethyl (meth)acrylate, and the like;halogenated (meth)acrylates such as pentabromobenzyl (meth)acrylate, andthe like; and acrylic or methacrylic amides such (meth)acrylamide,diacetone (meth)acrylamide, N(2-hydroxyethyl) (meth)acrylamide,N-methyl(meth)acrylamide, N-ethyl(meth)acrylamide,N,N-dimethyl(meth)acrylamide, N,N-dimethylaminopropyl(meth)acrylamide,N,N-dimethylaminopropyl(meth)acrylamide,N,N-dimethylaminoethyl(meth)acrylamide, and the like; and mixturescomprising at least one of the foregoing acryloyl monomers. It will beunderstood that the suffix (meth)acryl- denotes either acryl- ormethacryl-. Additional suitable acryloyl monomers are disclosed in U.S.Provisional Application Serial No. 60/262,571, filed Jan. 18, 2001.

In a preferred embodiment the acryloyl monomer is substantially free ofpolymerizable moieties other than acryloyl moieties. For example, inthis embodiment, the acryloyl monomer may not comprise an allylicmoiety, or a vinyl group directly bonded to an aromatic ring.

The composition may comprise the acryloyl monomer in an amount of atleast about 5 parts by weight, preferably at least about 10 parts byweight, per 100 parts by weight resin. The composition may comprise thepoly(arylene ether) in an amount up to about 60 parts by weight,preferably up to about 50 parts by weight, more preferably up to about40 parts by weight per 100 parts by weight resin.

The composition further comprises an allylic monomer. An allylic monomeris herein defined as a monomer comprising an allylic moiety having thestructure

wherein R²¹ may be hydrogen, C₁-C₆ alkyl, or the like. In a preferredembodiment, R²¹ is hydrogen. When the allylic monomer comprises at leasttwo allylic moieties, it is termed a polyfunctional allylic monomer.

Allylic monomers may include, for example, allylic alcohols, allylesters, allyl ethers, and alkoxylated allylic alcohols. Allylic alcoholsmay have the general structure

wherein R²² is hydrogen or C₁-C₆ alkyl. Suitable allylic alcoholsinclude allyl alcohol, methallyl alcohol, 2-ethyl-2-propen-1-ol, and thelike, and mixtures comprising at least one of the foregoing allylicalcohols.

Allyl esters may have the general structure

in which R²³ is hydrogen or C₁-C₆ alkyl, and R²⁴ is hydrogen or asaturated or unsaturated linear, branched, or cyclic C₁-C₃₀ alkyl, aryl,alkylaryl, or aralkyl group. Suitable allyl esters include, for example,allyl formate, allyl acetate, allyl butyrate, allyl benzoate, methallylacetate, allyl fatty esters, and the like, and mixtures comprising atleast one of the foregoing allyl esters.

Allyl ethers may have the general structure

wherein R²⁵ is hydrogen or C₁-C₆ alkyl, and R²⁶ is a saturated orunsaturated linear, branched, or cyclic C₁-C₃₀ alkyl, aryl, alkylaryl,or aralkyl group. Suitable allyl ethers include, for example, allylmethyl ether, allyl ethyl ether, allyl tert-butyl ether, allylmethylbenzyl ether, and the like, and mixtures comprising at least oneof the foregoing allyl ethers.

Allylic monomers further include alkoxylated allylic alcohols.Alkoxylated allylic alcohols may have the general structure

wherein R²⁷ is hydrogen or C₁-C₆ alkyl, A is an oxyalkylene group, andn, which is the average number of oxyalkylene groups in the alkoxylatedallylic alcohol, has a value from 1 to about 50. Oxyalkylene groups mayinclude oxyethylene, oxypropylene, oxybutylenes, and mixtures comprisingat least one of the foregoing oxyalkylene groups. Alkoxylated allylicalcohols can be prepared by reacting an allylic alcohol with up to about50 equivalents of one or more alkylene oxides in the presence of a basiccatalyst as described, for example, in U.S. Pat. Nos. 3,268,561 and4,618,703. Alkoxylated allylic alcohols can also be made by acidcatalysis, as described, for example, in Journal of the AmericanChemical Society, volume 71, pages 1152 ff. (1949).

In a preferred embodiment, the allylic monomer is a polyfunctionalallylic monomer. Specific polyfunctional allylic monomers include, forexample, diallyl adipate, diallyl citraconate, diallyl diglycolate,diallyl ether, diallyl fumarate, diallyl isophthalate, diallylitaconate, diallyl maleate, diallyl phthalate, diallyl terephthalate,triallyl aconitate, triallyl cyanurate, triallyl isocyanurate, triallylphosphate, triallyl trimellitate, tetraallyl o-silicic acid, and thelike, and mixtures comprising at least one of the foregoing allylicmonomers.

In one embodiment, the allylic monomer is substantially free ofpolymerizable moieties other than allylic moieties. In this embodiment,the allylic monomer may not comprise, for example, an acryloyl moiety,or a vinyl group directly bonded to an aromatic ring.

The composition may comprise the allylic monomer in an amount of atleast about 20 parts by weight, preferably at least about 30 parts byweight, more preferably at least about 40 parts by weight, per 100 partsby weight resin. The composition may comprise the allylic monomer in anamount up to about 80 parts by weight, preferably up to about 70 partsby weight, more preferably up to about 65 parts by weight, per 100 partsby weight resin.

The composition further comprises an abrasive filler. Such fillers mayhave a Knoop hardness of at least about 2,000, preferably at least about3,000, more preferably at least about 4,000, yet more preferably atleast about 5,000, even more preferably at least about 6,000. Suitablehard fillers may comprise, for example, aluminum oxides; siliconcarbides; silicon nitrides; sialons; cubic boron nitrides (CBN);aluminosilicates; titanium carbides; chromium carbides; tungstencarbides; zirconium oxides; silicon doped boron-aluminum-magnesium(BAM); natural and synthetic diamonds; garnets; composite ceramicscomprising at least one of the foregoing fillers; composite ceramicmetals (cermet) comprising a metal and at least one of the foregoingfillers, such as, for example, (tungsten carbide+cobalt) and (chromiumcarbide+nickel); combinations comprising at least one of the foregoingfillers; and the like. Presently preferred abrasive fillers includethose comprising diamond, CBN, and/or BAM.

There is no particular limitation on the particle size of the abrasivefiller. The abrasive filler may have a particle size corresponding toabout 600 mesh to about 5 mesh, preferably about 300 to about 25 mesh,more preferably about 200 to about 80 mesh.

In one embodiment, the abrasive filler comprises a metal coating. Themetal coatings may comprise, for example, Ni, Cu, Cr, Fe, Co, Sn, W, Ti,as well as alloys comprising at least one of the foregoing metals,mixtures comprising at least one of the foregoing metals, and the like.

The composition may comprise the abrasive filler in an amount of atleast about 5 parts by weight, preferably at least about 50 parts byweight, more preferably at least about 100 parts by weight, yet morepreferably at least about 200 parts by weight, ever more preferably atleast about 400 parts by weight, per 100 parts by weight resin. Thecomposition may comprise the abrasive filler in an amount of up to about2,000 parts by weight, preferably up to about 1,000 parts by weight,more preferably up to about 700 parts by weight, per 100 parts by weightresin. One advantage of the curable composition is its ability to allowhigh filler contents (higher than those permissible with phenolicresins) while maintaining excellent physical properties. Filler amountsmay also be expressed as volume percents of the total composition. Thus,the composition may comprise the abrasive filler in an amount of about 5to about 95 volume percent, preferably about 10 to about 90 volumepercent, more preferably about 50 to about 80 volume percent, based onthe total volume of the composition.

The composition may, optionally, further comprise secondary fillers.Secondary fillers may include, for example, abrasives such as ceramicborides, including titanium borides; thermal management particlesincluding, for example, powders comprising Cu, Fe, Sn, or bronze,mixtures of the foregoing metallic powders, and the like; additionalfillers such as carbon particles, carbon fibers, silicon, and the like,as well as alloys and mixtures comprising at least one of the foregoingsecondary fillers. In applications where electrical conductivity orstatic dissipation is desirable, preferred carbon fibers may includevapor-grown carbon fibers having an average diameter of about 3.5 toabout 500 nanometers as described in, for example, U.S. Pat. Nos.4,565,684 and 5,024,818 to Tibbetts et al.; 4,572,813 to Arakawa;4,663,230 and 5,165,909 to Tennent; 4,816,289 to Komatsu et al.;4,876,078 to Arakawa et al.; 5,589,152 to Tennent et al.; and 5,591,382to Nahass et al. The secondary fillers, when present, may be used in anamount of about 1 to about 30 parts by weight, per 100 parts by weightresin.

The composition may, optionally, further comprise a curing catalyst toincrease the curing rate of the unsaturated components. Curingcatalysts, also referred to as initiators, are used to initiate thepolymerization, cure or crosslink any of numerous thermoplastics andthermosets including unsaturated polyester, vinyl ester and allylicthermosets. Non-limiting examples of curing catalysts are thosedescribed in “Plastic Additives Handbook, 4^(th) Edition” R. Gachter andH. Muller (eds.), P. P. Klemchuck (assoc. ed.) Hansen Publishers, NewYork 1993 and in U.S. Pat. Nos. 5,407,972 to Smith et al., and 5,218,030to Katayose et al. The curing catalyst for the unsaturated portion ofthe thermoset would include any compound capable of producing radicalsat elevated temperatures. Such curing catalysts may include peroxy andnon-peroxy based radical initiators. Examples of useful peroxyinitiators include, for example, benzoyl peroxide, dicumyl peroxide,methyl ethyl ketone peroxide, lauryl peroxide, cyclohexanone peroxide,t-butyl hydroperoxide, t-butyl benzene hydroperoxide, t-butylperoctoate, 2,5-dimethylhexane-2,5-dihydroperoxide,2,5-dimethyl-2,5-di(t-butylperoxy)-hex-3-yne, di-t-butylperoxide,t-butylcumyl peroxide,alpha,alpha′-bis(t-butylperoxy-m-isopropyl)benzene,2,5-dimethyl-2,5-di(t-butylperoxy)hexane, dicumylperoxide,di(t-butylperoxy isophthalate, t-butylperoxybenzoate,2,2-bis(t-butylperoxy)butane, 2,2-bis(t-butylperoxy)octane,2,5-dimethyl-2,5-di(benzoylperoxy)hexane, di(trimethylsilyl)peroxide,trimethylsilylphenyltriphenylsilyl peroxide, and the like, as well asmixtures comprising at least one of the foregoing curing agents. Typicalnon-peroxy initiators include, for example,2,3-dimethyl-2,3-diphenylbutane,2,3-trimethylsilyloxy-2,3-diphenylbutane, and the like, and mixturescomprising at least one of the foregoing curing catalysts.

Those skilled in the art may determine an appropriate amount of curingcatalyst without undue experimentation. The curing catalyst amount maybe at least about 0.1 part by weight, preferably at least about 1 partby weight, more preferably at least about 2 part by weight, per 100parts by weight resin. The curing catalyst amount may be up to about 10parts by weight, preferably up to about 5 parts by weight, per 100 partsby weight resin. It is preferred that the identity and amount of thecuring catalyst be selected so as not to compromise the ability toprocess or maintain the curable formulation in powder form.

In addition to the components described above, the curable resincomposition may further comprise one or more additives such as flameretardants, flame retardant synergists, mold release agents and otherlubricants, antioxidants, thermal stabilizers, ultraviolet stabilizers,pigments, dyes, colorants, fibrous reinforcements, disc-shaped fillers,low-aspect ratio fillers, synthetic resins, natural resins,thermoplastic elastomers, and the like, as well as reaction products ofthe foregoing additives, and mixtures comprising at least one of theforegoing additives. Additive amounts may be determined without undueexperimentation. Non-limiting examples of additives are those describedin “Plastic Additives Handbook, 4^(th) Edition” R. Gachter and H. Muller(eds.), P. P. Klemchuck (assoc. ed.) Hansen Publishers, New York 1993.Many specific additives are also described in U.S. ProvisionalApplication Serial No. 60/262,571, filed Jan. 18, 2001.

In one embodiment, the composition is substantially free of alkenylaromatic monomers in which an alkenyl substituent is directly bonded toan aromatic ring. By substantially free of alkenyl aromatic monomers, itis meant that such monomers are not intentionally added. Such alkenylaromatic monomers include, for example, styrene, divinyl benzenes, andvinyl pyridine.

In one embodiment, the composition may be formulated as a powder. Forsome applications, it may be preferred that the powder be substantiallyfree of particles having any dimension greater than about 300micrometers, preferably substantially free of particles having anydimension greater than about 150 micrometers, more preferablysubstantially free of particles having any dimension greater than about100 micrometers, yet more preferably substantially free of particleshaving any dimension greater than about 50 micrometers. By substantiallyfree, it is meant that the composition includes less than 5% by weight,preferably less than 2% by weight, more preferably less than 1% byweight of particles having the specified dimensions. In one embodiment,the composition may be formulated as a mixture comprising curable resinparticles and abrasive filler particles, with the particle sizelimitations above applying only to the curable resin particles.

In another embodiment, the composition may be formulated as a pelletusing extrusion techniques known in the art.

In order to facilitate handling under ambient conditions and stabilityof powdered compositions under transportation conditions, it may bepreferred that the composition have a melting temperature of at leastabout 50° C., preferably at least about 60° C., more preferably at leastabout 70° C. To ensure melting below typical molding temperatures, itmay be preferred that the composition have a melting temperature up toabout 150° C., preferably up to about 140° C., more preferably up toabout 130° C.

In one embodiment, the curable resin composition comprises about 10 toabout 50 parts by weight of a poly(arylene ether); about 5 to about 60parts by weight of an acryloyl monomer; about 20 to about 80 parts byweight of an allylic monomer; and about 5 to about 2,000 parts by weightof an abrasive filler; wherein all parts by weight are based on 100parts by weight resin.

In one embodiment, the composition comprises about 15 to about 45 partsby weight of a capped poly(arylene ether); about 10 to about 40 parts byweight of a polyfunctional acryloyl monomer; about 30 to about 70 partsby weight of a polyfunctional allylic monomer; and about 100 to about1,000 parts by weight of an abrasive filler comprising silicon carbide,cubic boron nitride, synthetic diamond, or a mixtures comprising atleast one of the foregoing abrasive fillers; wherein all parts by weightare based on 100 parts by weight resin.

It will be understood that the composition encompasses reaction productsof any of the above-described curable compositions, as well as articlescomprising the cured compositions.

As the composition is defined as comprising multiple components, it willbe understood that each component is chemically distinct, particularlyin the instance that a single chemical compound may satisfy thedefinition of more than one component.

There is no particular limitation on the method used to prepared thecurable resin composition. In one embodiment, the composition may beprepared by a method comprising blending a poly(arylene ether), anallylic monomer, and an acryloyl monomer to form an intimate blend; andblending the intimate blend and an abrasive filler.

In one embodiment, the composition may be prepared by a methodcomprising blending a poly(arylene ether) and an allylic monomer to forma first intimate blend; blending the first intimate blend and anacryloyl monomer to form a second intimate blend; processing the secondintimate blend to form a curable powder; and blending the curable powderwith an abrasive filler. Processing the second intimate blend to form acurable powder may preferably comprise grinding the second intimateblend at a temperature up to about −75° C., preferably up to about −150°C., more preferably up to about −170° C., yet more preferably up toabout −190° C. Such temperatures embrittle the resin, therebyfacilitating grinding into small particles. For example, the resin maybe cryogenically ground by immersing in liquid nitrogen and allowing tocool to −196° C.; it may then be transferred rapidly into the opening ofa grinder in a portion-wise fashion where it may contact a rotatingscreen of the desired mesh size, passing through the mesh to acollection reservoir. Equipment to perform cryogenic grinding iscommercially available from, for example, Retsch/Brinkmann as the ZM-1Grinder. The method may further comprise blending the curable powderwith a curing catalyst.

In one embodiment, the composition may be prepared by a methodcomprising blending about 20 to about 80 parts by weight of an allylicmonomer with about 10 to about 50 parts by weight of a poly(aryleneether) to form a first intimate blend; blending the first intimate blendwith about 5 to about 60 parts by weight of an acryloyl monomer to forma second intimate blend; grinding the second intimate blend at atemperature up to about −75° C. to form a first curable powder; blendingthe first powder with a curing catalyst to form a second curable powder;and blending the second curable powder with about 5 to about 2000 partsby weight of an abrasive filler; wherein all parts by weight are basedon 100 parts by weight resin.

Processes useful for processing the composition include injectionmolding, co-injection molding, reaction injection molding, overmolding,resin transfer molding, vacuum assisted resin transfer molding, Seeman'scomposite resin infusion manufacturing process (SCRIMP), chemicallyassisted resin transfer molding, atmospheric pressure molding, open moldcasting, wet lay-up, dry lay-up, spray lay-up, sheet molding, bulkmolding, filament winding, pultrusion, lamination, and the like, andcombinations comprising at least one of the foregoing processes.Additional processes have been described in “Polyesters and TheirApplications” by Bjorksten Research Laboratories, Johan Bjorksten(pres.) Henry Tovey (Ch. Lit. Ass.), Betty Harker (Ad. Ass.), JamesHenning (Ad. Ass.), Reinhold Publishing Corporation, New York, 1956,“Uses of Epoxy Resins”, W. G. Potter, Newnes-Buttersworth, London 1975,“Chemistry and Technology of Cyanate Ester Resins” by I. Hamerton,Blakie Academic Publishing an Imprint of Chapman Hall.

There is no particular limitation on the method by which the compositionmay be cured. The composition may, for example, be cured thermally or byusing irradiation techniques, including UV irradiation and electron beamirradiation.

In one embodiment, the resin composition may be formulated as a powder.In this form, it is useful for mixing with other powdered additives toform a dry mix, in that blending is accomplished more readily than whenthe resin composition is a viscous liquid or paste. Use of the powderedresin composition is particularly advantageous when the adhesive fillercomprises the majority of the blend, for example about 70 to about 80weight percent of the total composition, the balance including thecurable resin.

In another embodiment, the resin composition may be formulated as apellet or other solid form derived from compounding. Compoundingprocedures known in the art may be useful to improve dispersion andwetting of the abrasive filler, compared to dispersion and wettingachieved with dry powder mixing methods. Dispersion and wetting ofabrasive fillers may also be improved by the use of coatings applied tothe abrasive filler.

Articles formed using the above processes may be post-mold processed,such as, for example, ground to a particular size or shape, sharpened,annealed, fixtured, or the like. In fact, there is no reason that bladescomprising the cured resin composition cannot be sharpened in use. Forexample, a lawnmower blade comprising the cured resin composition may besharpened should the blade become dull or nicked during use. There isvirtually no restriction as to the parts that can be made from thecurable and cured resin compositions. Presently preferred articlescomprising the cured composition include cut-off wheels and grindingwheels, and the like. For example, cut-off wheels molded from thecurable resin composition may exhibit a G ratio of at least about 300,preferably at least about 400, more preferably at least about 500, asmeasured on cemented tungsten carbide, where G ratio is the ratio(volume of work piece removed)/(volume of wheel consumed) as describedin “Metals Handbook; Ninth Edition; Volume 16—Machining” ASMInternational, page 422 (1989). A specific procedure for determining Gratio values is given in the following examples.

The curable and cured resin compositions are further illustrated by thefollowing non-limiting examples.

EXAMPLE 1

This example describes the preparation of a powdered resin material.Diallyl phthalate (510 grams; obtained from Aldrich as a liquid of 97%purity) was heated to 160-165° C. in a glass reaction vessel. To thiswas added methacrylate-capped poly(2,6-dimethyl-1,4-phenylene ether)(PPE-MA; 340 grams) having an intrinsic viscosity of 0.25 dL/g asmeasured at 25° C. in chloroform. The capped poly (arylene ether) wasprepared by reaction of the corresponding uncapped poly (arylene ether)with methacrylic anhydride, using procedures described in U.S. patentapplication Ser. No. 09/440,747, filed Nov. 16, 1999. The mixture wasstirred and heated until the poly(arylene ether) completely dissolved.Trimethylolpropane trimethacrylate (TMPTMA; 150 grams; obtained fromSartomeras a neat liquid) was then added to the reaction flask and mixeduntil it was completely blended. The solution was then poured into aflat container and allowed to cool so that it could form a hardened,wax-like substance. The resin mixture was cooled to −196° C. in liquidnitrogen and rapidly transferred to a Retsch/Brinkmann as the ZM-1Grinder where it was ground to produce a powdered resin having particlesizes less than about 50 grit. To the powdered resin was then added aninitiator, dicumyl peroxide, at 2 weight percent based on total resinweight.

EXAMPLE 2

This example describes the preparation of a curable compositionincluding an abrasive filler. Twenty parts by weight of the powderedresin of Example 1 were combined with 48.5 parts by weight ofnickel-coated diamond having 44 weight percent diamond and 56 weightpercent nickel, and 31.5 parts by weight of silicon carbide. Thenickel-coated diamond had a mesh size of 120-140. The above mixture wasplaced in a mold having a cavity of nominal dimensions 7 centimeterdiameter by 1 centimeter thickness. The mold was then closed and heatedto 140° C. as a force of 3 metric tons was applied to compress theresin/abrasive mixture. After 25 minutes, the specimen was removed fromthe mold and examined. A hardened, crosslinked, disk having goodphysical integrity was obtained. The sample exhibited a hardness usingRockwell indentor H of 91, a density by the Archimedes method of 100%(no porosity), and a room temperature thermal conductivity of 3.6 wattsper meter per Kelvin (W/m/K) indicating complete wetting and adhesion ofdiamond and silicon carbide grits by resin.

EXAMPLE 3

This example describes the preparation of a curable compositionincluding multiple abrasive fillers, as well as secondary fillers.Eighteen parts by weight of the powdered resin of Example 1 werecombined with 27 parts by weight diamond grit having a mesh size ofabout 120, 35 parts by weight of the nickel-coated diamond of Example 2,12 parts by weight of titanium boride fines having a mesh size of about−500, and 8 parts by weight of metallic copper fines having a mesh sizeof about −500. This mixture was placed into a mold having a cavity ofnominal dimensions 7 centimeters diameter by 1 centimeter thickness. Themold was closed and heated to 155° C. as a force of 6 metric tons wasapplied to compress the resin/abrasive mixture. After 30 minutes, thespecimen was removed from the mold and examined. A hardened, crosslinkeddisk having good physical integrity was obtained. The molded disk had aBarcol hardness of 66. The disk was post-cured for 20 hours at 150° C.The post-cured disk had a Barcol hardness of 73.

EXAMPLES 4 AND 5

These examples describe the use of an abrasive-filled composition tomold A1A abrasive cut-off wheels using two curing conditions. Theabrasive-filled curable composition of Example 3 was compression moldedat a temperature of about 350-375° F. and a pressure of about 20 ton/in²for 60 minutes to yield a 1A1 cut-off wheel having a wheel diameter of177.8 millimeters (7.0 inches), a wheel rim width of 6.4 millimeters(0.250 inches), and an abrasive rim depth of 6.4 millimeters (0.250inches). This grinding wheel corresponds to Example 4, and it had a bonddensity of 3.384 g/cc and an Rockwell Hardness H scale (HRH) value of68-74.

The composition and procedure used to prepare Example 4 was used toprepare Example 5, except that the curing temperature was increased toabout 700-750° F. and the pressure was increased to 15 ton/in². Thisgrinding wheel had a bond density of 3.297 g/cc and an HRH value of100-110.

Cut-off wheels were tested using tungsten carbide (WC) material. Wheelpreparation and test conditions are summarized in Table 1. Thecomposition and properties of the WC material are summarized in Table 2.Compositions, molding temperatures, and test results for the cut-offwheels are given in Table 3.

TABLE 1 ROUGH TRUING Rough Truing Device Brake Rough Truing 3.0 inchdiameter × 1.0 inch wide 37C60 MVK Silicon Wheel Carbide wheel RoughTruing 0.0002 inch - 0.0020 inch downfeed × 21.0 Conditions inch/mincrossfeed WHEEL DRESSING Dressing Stick Bay State 1.0 inch × 1.0 inchAluminum Oxide #9A240G9V82 Dress Mode Plunge Dress Plunge Rate 8inch/min Dress Amount 0.30 in³ FINISH TRUING Finish Truing Device BrakeFinish Truing Wheel 3.0 inch diameter × 0.090 inch wide MBS-750Metal-Bond Diamond wheel Mesh size 60/80 Concentration 10 volume %Truing Conditions 0.0001 inch downfeed × 16.0 inch/min crossfeed Numberof Passes 6 GRINDING TEST CONDITIONS Machine Brown & Sharpe model 8/24,15 hp CNC surface grinder Grind Mode Creepfeed (upcut) Wheel Speed 5,500feet/min (28 m/sec) Depth of Cut 0.040 inch (1.0 mm) Table Speed 7.5inch/min (2.3 m/min) Width of Cut 0.140 inch (3.6 mm) Length of Cut 3.50inch (89 mm) Material Removal Rate 0.30 in²/min (3.2 mm³/mm/sec)Workpiece Material Size 3.5 inch long × 0.140 inch wide (89 mm × 3.6 mmCoolant Master Chemical VHPE 320 water soluble oil at 5% concentrationCoolant Flow 24 gallons/min at 100 psi (entry and exit nozzles)

TABLE 2 Properties Designations Transverse ISO US Compositions (Wt. %)Density Avg Grain Hardness Rupture Symbol Code Equiv. WC TiC Ta(Nb) Cog/cm³ Size μm HRA Strength (psi) T-11 P30 C5 72 11.5 8.5 8.5 12.4 2 91.4250,000

TABLE 3 Example 3 Example 4 COMPOSITION diallyl phthalate (pbw) 51 51PPE-MA (pbw) 34 34 TMPTMA (pbw) 15 15 dicumyl peroxide 2 2 diamond 150150 nickel-coated diamond 194 194 titanium boride 67 67 copper 44 44CURING TEMPERATURE (° F.) 350-375 700-750 PROPERTIES G-ratio, 1 in³ 393583 Power (kW) 1.9 2.1 Ra (micrometer-inch) 21 13

The results in Table 1 show that cut-off wheels prepared from thecurable resin composition exhibit low wear rate, high free-cuttingcapability, and excellent surface finish.

While the invention has been described with reference to a preferredembodiment, it will be understood by those skilled in the art thatvarious changes may be made and equivalents may be substituted forelements thereof without departing from the scope of the invention. Inaddition, many modifications may be made to adapt a particular situationor material to the teachings of the invention without departing fromessential scope thereof. Therefore, it is intended that the inventionnot be limited to the particular embodiment disclosed as the best modecontemplated for carrying out this invention, but that the inventionwill include all embodiments falling within the scope of the appendedclaims.

All cited patents and other references are incorporated herein byreference in their entirety.

What is claimed is:
 1. A curable resin composition, comprising: apoly(arylene ether); an acryloyl monomer; an allylic monomer; and anabrasive filler selected from the group consisting of silicon carbides;silicon nitrides; sialons; cubic boron nitrides; aluminosilicates;titanium carbides; chromium carbides; tungsten carbides; zirconiumoxides; silicon doped boron-aluminum-magnesium; natural and syntheticdiamonds; garnets; composite ceramics comprising at least one of theforegoing abrasive fillers; composite ceramic metals comprising a metaland at least one of the foregoing abrasive fillers; and combinationscomprising at least one of the foregoing abrasive fillers.
 2. Thecurable resin composition of claim 1, wherein the poly(arylene ether)comprises a plurality of structural units of the formula

wherein for each structural unit, each Q¹ is independently selected fromthe group consisting of halogen, primary or secondary C₁-C₁₂ alkyl,phenyl, C₁-C₁₂ haloalkyl, C₁-C₁₂ aminoalkyl, C₁-C₁₂ hydrocarbonoxy, andC₁-C₁₂ halohydrocarbonoxy wherein at least two carbon atoms separate thehalogen and oxygen atoms; and each Q² is independently selected from thegroup consisting of hydrogen, halogen, primary or secondary C₁-C₁₂alkyl, phenyl, C₁-C₁₂ haloalkyl, C₁-C₁₂ aminoalkyl, C₁-C₁₂hydrocarbonoxy, and C₂-C₁₂ halohydrocarbonoxy wherein at least twocarbon atoms separate the halogen and oxygen atoms.
 3. The curable resincomposition of claim 1, wherein the poly(arylene ether) has a freehydroxyl group content less than about 500 micrograms per gram.
 4. Thecurable resin composition of claim 1, wherein the poly(arylene ether)comprises a capped poly(arylene ether) having the structure Q-(J-K)_(y)wherein Q is the residuum of a monohydric, dihydric, or polyhydricphenol; y is 1 to 100; J comprises recurring units having the structure

wherein R¹-R⁴ are each independently selected from the group consistingof hydrogen, halogen, primary or secondary C₁-C₁₂ alkyl, C₂-C₁₂ alkenyl,C₂-C₁₂ alkynyl, C₁-C₁₂ aminoalkyl, C₁-C₁₂ hydroxyalkyl, phenyl, C₁-C₁₂haloalkyl, C₁-C₁₂ aminoalkyl, C₁-C₁₂ hydrocarbonoxy, and C₂-C₁₂halohydrocarbonoxy wherein at least two carbon atoms separate thehalogen and oxygen atoms; m is 1 to about 200; and K is a capping groupselected from the group consisting of

wherein R⁵ is C₁-C₁₂ alkyl; R⁶-R⁸ are each independently selected fromthe group consisting of hydrogen, C₁-C₁₂ alkyl, C₂-C₁₂ alkenyl, C₆-C₁₈aryl, C₇-C₁₈ mixed (alkyl-aryl), C₂-C₁₂ alkoxycarbonyl, C₇-C₁₈aryloxycarbonyl, C₈-C₁₈ mixed (alkyl-aryl)oxycarbonyl, nitrile, formyl,carboxylate, imidate, and thiocarboxylate; R⁹-R¹³ are each independentlyselected from the group consisting of hydrogen, halogen, C₁-C₁₂ alkyl,hydroxy, and amino; and wherein Y is a divalent group selected from thegroup consisting of

wherein R¹⁴ and R¹⁵ are each independently selected from the groupconsisting of hydrogen and C₁-C₁₂ alkyl.
 5. The curable resincomposition of claim 4, wherein the capped poly(arylene ether) comprisesa capping group having the structure

wherein R⁶-R⁸ are each independently selected from the group consistingof hydrogen, C₁-C₁₂ alkyl, C₂-C₁₂ alkenyl, C₆-C₁₈ aryl, C₇-C₁₈ mixed(alkyl-aryl), C₂-C₁₂ alkoxycarbonyl, C₇-C₁₈ aryloxycarbonyl, C₈-C₁₈mixed (alkyl-aryl)oxycarbonyl, nitrile, formyl, carboxylate, imidate,and thiocarboxylate.
 6. The curable resin composition of claim 4,wherein the capped poly(arylene ether) is prepared by capping apoly(arylene ether) consisting essentially of the polymerization productof at least one monohydric phenol having the structure

wherein R¹-R⁴ are each independently selected from the group consistingof hydrogen, halogen, primary or secondary C₁-C₁₂ alkyl, C₂-C₁₂ alkenyl,C₂-C₁₂ alkynyl, C₁-C₁₂ aminoalkyl, C₁-C₁₂ hydroxyalkyl, phenyl, C₁-C₁₂haloalkyl, C₁-C₁₂ aminoalkyl, C₁-C₁₂ hydrocarbonoxy, and C₂-C₁₂halohydrocarbonoxy wherein at least two carbon atoms separate thehalogen and oxygen atoms.
 7. The curable resin composition of claim 1,wherein the poly(arylene ether) has an intrinsic viscosity of about 0.1to about 0.5 deciliters/gram in chloroform at 25° C.
 8. The curableresin composition of claim 1, comprising about 10 to about 50 parts byweight of the poly(arylene ether) per 100 parts by weight resin.
 9. Thecurable resin composition of claim 1, wherein the acryloyl monomercomprises at least one acryloyl moiety having the structure

wherein R¹⁶ and R¹⁷ are each independently selected from the groupconsisting of hydrogen and C₁-C₁₂ alkyl, and wherein R¹⁶ and R¹⁷ may bedisposed either cis or trans about the carbon-carbon double bond. 10.The curable resin composition of claim 1, wherein the acryloyl monomercomprises at least one acryloyl moiety having the structure

wherein R¹⁸-R²⁰ are each independently selected from the groupconsisting of hydrogen, C₁-C₁₂ alkyl, C₂-C₁₂ alkenyl, C₆-C₁₈ aryl,C₇-C₁₈ mixed (alkyl-aryl), C₂-C₁₂ alkoxycarbonyl, C₇-C¹⁸aryloxycarbonyl, mixed C⁸-C¹⁸ (alkyl-aryl)oxycarbonyl, nitrile, formyl,carboxylate, imidate, and thiocarboxylate.
 11. The curable resincomposition of claim 10, wherein the acryloyl monomer comprises at leasttwo acryloyl moieties.
 12. The curable resin composition of claim 1,wherein the acryloyl monomer is selected from the group consisting oftrimethylolpropane trimethacrylate, trimethylolpropane triacrylate,1,6-hexanediol dimethacrylate, 1,6-hexanediol diacrylate, ethyleneglycol dimethacrylate, ethylene glycol diacrylate, propylene glycoldimethacrylate, propylene glycol diacrylate, cyclohexanedimethanoldimethacrylate, cyclohexanedimethanol diacrylate, butanedioldimethacrylate, butanediol diacrylate, diethylene glycol dimethacrylate,diethylene glycol diacrylate, triethylene glycol dimethacrylate,triethylene glycol diacrylate, isobornyl methacrylate, isobornylacrylate, methyl methacrylate, methyl acrylate, and mixtures comprisingat least one of the foregoing acryloyl monomers.
 13. The curable resincomposition of claim 1, wherein the acryloyl monomer is selected fromthe group consisting of trimethylolpropane trimethacrylate,trimethylolpropane triacrylate, and mixtures comprising at least one ofthe foregoing acryloyl monomers.
 14. The curable resin composition ofclaim 1, wherein the acryloyl monomer is substantially free ofpolymerizable moieties other than acryloyl moieties.
 15. The curableresin composition of claim 1, comprising about 5 to about 60 parts byweight of the acryloyl monomer per 100 parts by weight resin.
 16. Thecurable resin composition of claim 1, comprising about 5 to about 40parts by weight of the acryloyl monomer per 100 parts by weight resin.17. The curable resin composition of claim 1, wherein the allylicmonomer comprises an allylic moiety having the structure

wherein R²¹ is selected from the group consisting of hydrogen and C₁-C₆alkyl.
 18. The curable resin composition of claim 17, wherein theallylic monomer comprises at least two allylic moieties.
 19. The curableresin composition of claim 1, wherein the allylic monomer is selectedfrom the group consisting of allyl alcohol, methallyl alcohol,2-ethyl-2-propen-1-ol, allyl formate, allyl acetate, allyl butyrate,allyl benzoate, methallyl acetate, allyl fatty esters, allyl methylether, allyl ethyl ether, allyl tert-butyl ether, allyl methylbenzylether, alkoxylated allylic alcohols, diallyl adipate, diallylcitraconate, diallyl diglycolate, diallyl ether, diallyl fumarate,diallyl isophthalate, diallyl itaconate, diallyl maleate, diallylphthalate, diallyl terephthalate, triallyl aconitate, triallylcyanurate, triallyl isocyanurate, triallyl phosphate, triallyltrimellitate, tetraallyl o-silicic acid, and mixtures comprising atleast one of the foregoing allylic monomers.
 20. The curable resincomposition of claim 1, wherein the allylic monomer is selected from thegroup consisting of diallyl adipate, diallyl citraconate, diallyldiglycolate, diallyl ether, diallyl fumarate, diallyl isophthalate,diallyl itaconate, diallyl maleate, diallyl phthalate, diallylterephthalate, triallyl aconitate, triallyl cyanurate, triallylisocyanurate, triallyl phosphate, triallyl trimellitate, tetraallylo-silicic acid, and mixtures comprising at least one of the foregoingallylic monomers.
 21. The curable resin composition of claim 1, whereinthe allylic monomer comprises diallyl phthalate.
 22. The curable resincomposition of claim 1, wherein the allylic monomer is substantiallyfree of polymerizable moieties other than allylic moieties.
 23. Thecurable resin composition of claim 1, comprising about 20 to about 80parts by weight of the allylic monomer per 100 parts by weight resin.24. The curable resin composition of claim 1, wherein the abrasivefiller has a Knoop hardness of at least about 2,000.
 25. The curableresin composition of claim 1, wherein the abrasive filler has a meshsize of about 600 to about
 5. 26. The curable resin composition of claim1, wherein the abrasive filler comprises a metal coating.
 27. Thecurable resin composition of claim 26, wherein the metal coatingcomprises a metal selected from the group consisting of Ni, Cu, Cr, Fe,Co, Sn, W, Ti, alloys comprising at least one of the foregoing metals,and mixtures comprising at least one of the foregoing metals.
 28. Thecurable resin composition of claim 1, wherein the abrasive filler isselected from the group consisting of silicon carbides; cubic boronnitrides; natural and synthetic diamonds; composite ceramic metalscomprising a metal and at least one of the foregoing fillers; andcombinations comprising at least one of the foregoing abrasive fillers.29. The curable resin composition of claim 1, comprising up to about2,000 parts by weight of the abrasive filler per 100 parts by weightresin.
 30. The curable resin composition of claim 1, comprising at leastabout 5 parts by weight of the abrasive filler per 100 parts by weightresin.
 31. The curable resin composition of claim 1, comprising at leastabout 300 parts by weight of the abrasive filler per 100 parts by weightresin.
 32. The curable resin composition of claim 1, comprising at leastabout 400 parts by weight of the abrasive filler per 100 parts by weightresin.
 33. The curable resin composition of claim 1, further comprisinga secondary filler selected from the group consisting of ceramicborides, Cu, Fe, Sn, bronze, C, silica, alumina, Si, and mixturescomprising at least one of the foregoing secondary fillers.
 34. Thecurable resin composition of claim 1, further comprising a curingcatalyst.
 35. The curable resin composition of claim 34, wherein thecuring catalyst is selected from the group consisting of benzoylperoxide, dicumyl peroxide, methyl ethyl ketone peroxide, laurylperoxide, cyclohexanone peroxide, t-butyl hydroperoxide, t-butyl benzenehydroperoxide, t-butyl peroctoate,2,5-dimethylhexane-2,5-dihydroperoxide,2,5-dimethyl-2,5-di(t-butylperoxy)-hex-3-yne, di-t-butylperoxide,t-butylcumyl peroxide,alpha,alpha′-bis(t-butylperoxy-m-isopropyl)benzene,2,5-dimethyl-2,5-di(t-butylperoxy)hexane, dicumylperoxide,di(t-butylperoxy isophthalate, t-butylperoxybenzoate,2,2-bis(t-butylperoxy)butane, 2,2-bis(t-butylperoxy)octane,2,5-dimethyl-2,5-di(benzoylperoxy)hexane, di(trimethylsilyl)peroxide,trimethylsilylphenyltriphenylsilyl peroxide,2,3-dimethyl-2,3-diphenylbutane,2,3-trimethylsilyloxy-2,3-diphenylbutane, and mixtures comprising atleast one of the foregoing curing catalysts.
 36. The curable resincomposition of claim 34, comprising about 0.1 to about 10 parts byweight of the curing catalyst per 100 parts by weight resin.
 37. Thecurable resin composition of claim 1, further comprising an additiveselected from the group consisting of flame retardants, flame retardantsynergists, mold release agents and other lubricants, antioxidants,thermal stabilizers, ultraviolet stabilizers, pigments, dyes, colorants,anti-static agents, fibrous reinforcements, disc-shaped fillers,low-aspect ratio fillers, synthetic resins, natural resins,thermoplastic elastomers, and mixtures comprising at least one of theforegoing additives.
 38. The curable resin composition of claim 1,wherein the composition is substantially free of alkenyl aromaticmonomers in which an alkenyl substituent is directly bonded to anaromatic ring.
 39. The curable resin composition of claim 1, having amelting point of about 50° C. to about 150° C.
 40. The curable resincomposition of claim 1, in the form of a powder.
 41. The curable resincomposition of claim 40, wherein the powder is substantially free ofnon-abrasive particles having any dimension greater than about 300micrometers.
 42. The curable resin composition of claim 1, in the formof a pellet.
 43. A curable resin composition, comprising: about 10 toabout 50 parts by weight of a poly(arylene ether); about 5 to about 60parts by weight of an acryloyl monomer; about 20 to about 80 parts byweight of an allylic monomer; and about 5 to about 2,000 weight percentof an abrasive filler selected from the group consisting of siliconcarbides; silicon nitrides; sialons; cubic boron nitrides;aluminosilicates; titanium carbides; chromium carbides; tungstencarbides; zirconium oxides; silicon doped boron-aluminum-magnesium;natural and synthetic diamonds; garnets; composite ceramics comprisingat least one of the foregoing abrasive fillers; composite ceramic metalscomprising a metal and at least one of the foregoing abrasive fillers;and combinations comprising at least one of the foregoing abrasivefillers; wherein all parts by weight are based on 100 parts by weightresin.
 44. A curable resin composition, comprising: about 15 to about 45parts by weight of a capped poly(arylene ether); about 10 to about 40parts by weight of a polyfunctional acryloyl monomer; about 30 to about70 parts by weight of a polyfunctional allylic monomer; and about 100 toabout 1,000 parts by weight of an abrasive filler comprising siliconcarbide, cubic boron nitride, or synthetic diamond; wherein all parts byweight are based on 100 parts by weight resin.
 45. A cured resincomposition, comprising the reaction product of: a poly(arylene ether);an acryloyl monomer; an allylic monomer; and an abrasive filler selectedfrom the group consisting of silicon carbides; silicon nitrides;sialons; cubic boron nitrides; aluminosilicates; titanium carbides;chromium carbides; tungsten carbides; zirconium oxides; silicon dopedboron-aluminum-magnesium; natural and synthetic diamonds; garnets;composite ceramics comprising at least one of the foregoing abrasivefillers; composite ceramic metals comprising a metal and at least one ofthe foregoing abrasive fillers; and combinations comprising at least oneof the foregoing abrasive fillers.
 46. A method of preparing a curableresin composition, comprising: blending a poly(arylene ether), anallylic monomer, and an acryloyl monomer to form an intimate blend; andblending the intimate blend and an abrasive filler selected from thegroup consisting of silicon carbides; silicon nitrides; sialons; cubicboron nitrides; aluminosilicates; titanium carbides; chromium carbides;tungsten carbides; zirconium oxides; silicon dopedboron-aluminum-magnesium; natural and synthetic diamonds; garnets;composite ceramics comprising at least one of the foregoing abrasivefillers; composite ceramic metals comprising a metal and at least one ofthe foregoing abrasive fillers; and combinations comprising at least oneof the foregoing abrasive fillers.
 47. A method of preparing a curableresin composition, comprising: blending a poly(arylene ether) and anallylic monomer to form a first intimate blend; blending the firstintimate blend and an acryloyl monomer to form a second intimate blend;processing the second intimate blend to form a curable powder; andblending the curable powder with an abrasive filler.
 48. The method ofclaim 47, wherein processing the second intimate blend to form a curablepowder comprises grinding at a temperature up to about −75° C.
 49. Themethod of claim 47, further comprising blending the curable powder witha curing catalyst.
 50. A method of preparing a curable resincomposition, comprising: blending about 20 to about 80 parts by weightof an allylic monomer with about 10 to about 50 parts by weight of apoly(arylene ether) to form a first intimate blend; blending the firstintimate blend with about 5 to about 60 parts by weight of an acryloylmonomer to form a second intimate blend; grinding the second intimateblend at a temperature less than about −75° C. to form a first curablepowder; blending the first powder with a curing catalyst to form asecond curable powder; and blending the second curable powder with about5 to about 2000 parts by weight of an abrasive filler; wherein all partsby weight are based on 100 parts by weight resin.